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Two high-profile critics of former President Trump achieved significant court wins on the start of the week when a US judge dismissed the federal indictments against them.

For weeks since their indictments, former FBI Director James Comey and New York Attorney General Letitia James have insisted vehemently that they are not guilty, asserting that the president and justice department are simply singling out them for retaliation.

Federal Judge Cameron Currie tossed the charges against them due to attorney Lindsey Halligan's improper appointment as federal prosecutor. But she also left open the possibility for the government to try again.

• Judge dismisses charges against ex-FBI director Comey and NY attorney general James
• Federal judge states DOJ errors may have tainted the Comey trial
• What is ex-FBI director James Comey charged with?

Comey admitted that likelihood after the ruling, stating he thinks Trump will probably come after him again.

And White House spokeswoman Abigail Jackson seemed to confirm it: This isn't the last chapter on this issue.

But the government faces steep obstacles to effectively try either after this setback, and legal analysts hesitate to predict what could happen next due to the unprecedented circumstances of the cases.

It feels to me like uncharted territory, said Kay Levine, Emory University School of Law professor.

Could the justice department appeal?

The DOJ can challenge the judge's decision before a federal appeals court. In this case, that would be the Fourth Circuit Appeals Court.

US Attorney General Pam Bondi signaled she would take this route, pledging to use all available legal action, including an expedited appeal.

Previously, the Trump administration has aggressively appealed unfavourable rulings, taking cases from lower courts and sometimes fast-tracking its petitions up to the Supreme Court.

Abbe Lowell, an attorney representing James, vowed to continue to challenge any further politically driven indictments through every lawful means available.

In the event of an appeals process, the DOJ likely would have its own attorneys argue the case, making Halligan's role in the appeal unclear.

Is it possible there be fresh indictments?

The federal prosecutors charged Comey with lying to lawmakers and obstruction of justice. Federal prosecutors charged James with financial fraud and providing false information to a financial institution.

Each pleaded not guilty. In addition to claiming Halligan was unlawfully appointed, both also claimed to be targets of retaliatory legal action.

Since the initial charges were dismissed (though, of course, appeals could change that), the government might try to convene fresh grand juries and secure new charges.

Based on my analysis, a different attorney could bring James' case to a new grand jury and get a fresh indictment, stated Ms Levine.

But legal expert John Day, head of the American College of Trial Lawyers, said it could be a complex process – certainly in the Comey matter.

It's clear that it will be hotly contested, whether Mr Comey's case can be re-indicted if a properly assigned attorney is assigned and is can obtain an indictment.

He described the tangle of attorneys, courts, and motions involved as a procedural morass with no simple answers.

It could be more difficult for the government to try to bring the exact same charges against James Comey.

One problem is the statute of limitations – the deadline that prosecutors had to charge him for these specific allegations – which expired at the end of September. Nonetheless, the dismissal of the charges would activate a half-year extension for the DOJ to bring the case again.

Even so in that case, his lawyers said it intends to argue the prosecution is out of time.

The decision further indicates that because the indictment is void, the statute of limitations has run and there can be no further indictment, attorney Patrick Fitzgerald said on Monday.

What happens to prosecutor Lindsey Halligan?

In both decisions on the charges against Comey and James, the judge was blunt: Halligan was wrongly appointed.

The judge stated in the James ruling that the Attorney General's attempt to install Halligan as Interim US Attorney for the Virginia Eastern District was invalid.

Therefore, she had no lawful authority to file the charges, she wrote.

US attorneys are proposed by the president and require Senate approval. US laws regulate how people can be appointed on a interim basis, but the judge determined that Halligan's appointment had breached these regulations.

That leaves Halligan's position on future cases against both individuals, again, uncertain.

The ruling also could raise doubts on any other cases Halligan has prosecuted in the Virginia Eastern District where she serves.

But Attorney General Bondi said on that day that she designated Halligan a special federal prosecutor and commended her work as excellent.

The White House stood by its stance that Halligan's appointment was legal, spokesperson Karoline Leavitt told reporters on Monday.